


The Blood Of The Covenant

by Bajada



Category: Supernatural
Genre: Alcohol, Bar Owner Lee Webb, Dean Loves Getting Praised, Doctor Billie, Enemies to Lovers, F/M, Helpful Rowena MacLeod, Implied/Referenced Blow Jobs, Italian Mafia, John Winchester's A+ Parenting, M/M, Mafia AU, Major Illness, Mary Winchester Being an Asshole, Past Lee Webb/Dean Winchester, Russian Mafia, Slow Burn, Smoker Dean Winchester, Strippers & Strip Clubs, Winchester Mafia Family, that'll come up more later
Language: English
Status: In-Progress
Published: 2020-09-29
Updated: 2020-10-12
Packaged: 2021-03-08 03:55:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 11,648
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26719411
Author URL: https://archiveofourown.org/users/Bajada/pseuds/Bajada
Summary: The Winchester Dynasty will never fall.At least, that's what John and Mary, heads of the most powerful crime family in the city believe. They have built their empire from nothing, and are willing to do whatever it takes to maintain their control.When a new family, the Novaks, threaten the delicate balance of power they have maintained for years, the eldest son, Dean, is tasked with infiltrating the ranks of the Novak's organization to destroy them from the inside.Dean has always been a soldier in his parent's wars, never questioning where his loyalties lie, but when he comes face to face with Castiel Novak, one of the sons of the family threatening to destroy his own, he wonders if maybe there could be more to life than he believed. Maybe this blue-eyed stranger can offer in the ticket out he never knew he wanted.They say that the blood of the covenant runs thicker than the water of the womb, but how do you turn your back on family? Will Dean choose love over loyalty? Will he leave behind all he's ever known? Or are he and Castiel destined to just be pawns in the war for power that rules the city's underworld?
Relationships: Castiel/Dean Winchester, Jessica Moore/Sam Winchester, John Winchester/Mary Winchester, Lee Webb/Dean Winchester
Comments: 18
Kudos: 39





	1. Dinner

**Author's Note:**

> Hello, dear reader. Welcome to the journey of "The Blood of the Covenant". This is a work in progress, and as such, I don't know where it's going to end up. Because of this, I URGE YOU to read the tags carefully with every new chapter update as the WILL change. I have a *vague* idea of where I want to be at the end, but things could change. If you see anything in the tags that you don't think should be there, or you'd like to suggest that a tag be added/changed, please message me.
> 
> I know this is going to be a long one, so bear with me, but I hope you enjoy reading this as much as I've enjoyed writing it so far. If you'd like to follow me over on tumblr, I'm [@bktynes-writes](https://www.tumblr.com/blog/bktynes-writes) and would love to interact there. I also made some graphics to go along with this fic, which you can find [here](https://bktynes-writes.tumblr.com/post/630624312713527296/so-as-per-the-fantastic-advice-of-the-wonderful). The fic itself was inspired by the "family portrait" style photo at the top.
> 
> Thanks again, and without further ado, on to the fic!

The city at night always had a certain charm about it that Dean couldn't put his finger on. Maybe it was the way everything lit up a bit more or the fact that the darkness hid the grime that clung to every surface like a second skin, but the alleyways and culverts of the buildings seemed more inviting when they were filled with shadow.

He loved this city. Every dirty stairwell, every seedy bar, every doorway that led to nowhere, Dean knew them all. He had grown up on these streets, and he wouldn't change it for the world.

The sound of a car horn brought him back to reality, pulling him out of his nostalgic reverie and into the moment. He looked down at his dress shoes, sparkling in the neon lights against the damp pavement, and smiled. If there was one thing Dean Winchester knew how to do, it was dress to impress. His father had instilled in him that first impressions were important at a very young age, and how a man looks could change the direction of any transaction.

Tonight was the first Sunday of the month, which meant dinner with the Family at Cain's. Dean never looked forward to these dinners - he found them to be mundane - but as the eldest son of the most powerful crime family in the city, he knew his mother and father expected him to attend.

Thus, he found himself in his best suit, pulling open the restaurant's glass door and striding past the host stand like he owned the place. The young woman there gave him a nervous look, and he shot her his most charming smile, causing her to duck her head as a deep red blush crept up her cheeks. He passed by the other tables and made his way to the back of the restaurant, pointedly ignoring the stares and whispers that followed him from the other patrons. He was used to this behaviour. Anyone who was anyone in the city recognized the Winchesters, and their reputation preceded them.

He made his way past the kitchen, stopping briefly to say hello to Cain, clapping him on the shoulder.

"Dean!" Cain exclaimed, turning around and pulling him into a rib-crushing hug. "I didn't think you were gonna show! Everyone else is already here."

Dean laughed. In another life, he would have called him a friend.

But Winchesters didn't have friends.

"Yeah, I figured they would be." He said. "What can I say? Fashionably late is kinda my style." He shrugged and smiled.

"That's my boy, always gotta make an entrance." Cain beamed at him. "They're in the back room. I'll get your usual added to the order. Hurry up before your dad tears a strip off you!"

"Thanks, Cain," Dean said. He ducked past him and headed to the very back of the dining room.

Dean could now see the usual suspects gathered around their regular table. He spotted Bobby gruffly speaking to Ellen Harvelle and her daughter Jo. The Harvelles were powerful associates who owned many of the bars and rest stops along the freeway into the city, and Dean's father liked to keep them close because he had been friends with Ellen's late husband, Bill.

Ellen was a good source of information for the family. People let information slip that they shouldn't after a few rounds of shots at one of Ellen's roadhouses, and she and Jo had ears like bats. Dean was pretty sure the main reason she was included in these clandestine meetings of the family, though, is that his parents, despite their vehement claims otherwise, were a little bit afraid of her. He couldn't blame them. He had grown up with Jo and, despite being six years older, had had his ass handed to him more times than he could count by the feisty blonde.

Dean chuckled to himself at the memory as he slid quietly into the seat next to his younger brother, Sam.

"You're late," stated the younger of the Winchester brothers, his arm draped lazily across his girlfriend Jessica's shoulders.

"Yeah, I was over at the mill. Gordon owes us and is being...difficult." He reached for the bottle of wine that sat on the table and filled his glass. He wasn't usually a fan of wine, but Cain always brought out the good bottles for these meetings, and when he didn't have to pay, it would be rude to refuse.

"Dad is gonna be pissed." Said Sam, finishing his own glass and holding it out for Dean to refill.

"No, he won't," Dean replied, pouring too much wine into his brother's glass. "He knows how Gordon is. He'll just be glad I didn't break too many of his fingers to get him to agree to pay his dues."

"Whatever you say, Dean," Sam replied, rolling his eyes. He ran his fingers through his absurdly long hair, and Dean found himself itching to strap his brother into a barber's chair and order a buzz cut.

A clink of cutlery against glass brought the assembly to silence and drew everyone's attention to the man standing at the head of the table. John Winchester was an imposing figure at the best of times, and his broad shoulders, clad in the threads of his fine Italian suit, added to his commanding demeanour. His neatly trimmed beard was flecked with grey, as was the perfectly slicked hair on his head. He stood with pride and demanded the respect of those around him with ease.

"Now that my son has finally decided to grace us with his presence, we can call this meeting to order," John spoke with an air of distaste directed solely at Dean.

"Ah, you know me pops, better late than never," Dean said nonchalantly. Sam was right; John was pissed.

"Indeed," said his father coolly.

Dean tuned out most of the ensuing conversations. It was the typical discussion of territory, who was responsible for handling the gang activity on the west side, who was collecting from which businesses for protection owed and whether or not they had paid (Dean received a small nod of approval from John when he informed the table that Gordon would no longer be causing issues).

When the food came, Dean was treated to the most delicious looking plate of carbonara he had ever seen. Cain truly did know the way to his heart. Before he had the chance to dig in, a noise from the opposite end of the table drew everyone's attention.

A beautiful woman with wavy brown hair rose from the table, and Dean rolled his eyes, huffing dramatically into his chair. Bela Talbot was always trying to draw attention to herself at these meetings, and tonight would be no exception. She wasn't, strictly speaking, part of the Family, but she was part of a necessary evil alliance that the Winchesters had forged years ago to have hands in the art trade, and Dean had found her to be nothing but a nuisance ever since.

Her words dripped with a caramel sweetness, and despite his intense dislike of the woman, Dean couldn't help but stare at her as she spoke.

"John. Mary. Dear Winchester Family. It has come to my attention that there appears to be a new family on the North shore. They arrived from New Jersey about six weeks ago and have been a thorn in my side ever since." She scowled.

"Why hasn't it been dealt with, Bela?" Asked Sam. "The North shore is your territory, isn't it?" Sam was flexing his powers a little bit, addressing Bela that way. Usually, it would be up to John to chastise her for not taking care of a threat to their operations, but Dean could see the look of pride in his father's eyes at Sam stepping in so willingly.

Bela's face tinged pink slightly at the admonishing tone in Sam's voice, and she puffed her cheeks out before speaking out again. "Under regular circumstances, Samuel, I would, but it seems that these Novaks are a bit better at playing cat and mouse than I would have anticipated."

"Novak?" Dean snorted. "What is that, Polish?"

Bela glared at him. "I believe it's Serbian, actually."

Dean shrugged and twisted his fork idly in his pasta, hoping she would get to the point before it got cold. Sam continued to address her. "What's the problem, Bela?"

"They've taken out three of my warehouses since their arrival, and the attendance at both the craps game and the pool hall is down by thirty-two percent." She sighed, and Dean perked up. He almost wanted to shake the hand of anyone who could cause Bela this much distress, but this was clearly an attack on the family's assets. "Half the shops on Arthur Street aren't paying their fees because the Novaks have started charging them, and when I sent Ruby over to persuade them, she came back bloody and threatening to skip town."

Dean's smile faded as quickly as it had appeared. Ruby was savage in the art of 'persuasion,' and he could hardly imagine anyone getting the better of her. He leaned forward, his brow furrowed. A new family trying to start a war with the Winchesters? The last time that had happened, Dean was a teenager, and, much to his dismay, his parents had insisted he not be involved. He had watched helplessly from inside the Catholic boy's school his father had shipped him to, as his people were shot in the street.

But Dean was in his thirties now, and the prospect of war looming on the horizon made him giddy with anticipation.

Mary Winchester, who had been quietly observing her husband and sons until this point, suddenly cleared her throat, which made all the men at the table sit up a little straighter. She was a fierce-looking woman with high cheekbones, a square jaw, and deep eyes, all framed by locks of cascading blonde curls. It was easy to see where her sons had gotten their charming good looks from.

She sat forward and touched her husband's forearm gently. "Bela. While I'm sure the loss of your warehouses is devastating, no one would be foolish enough to start a war with our family." She smiled. "And if Ruby and the girls from Rowena's can't handle what is being asked of them, then perhaps it is time to remind them who it is they work for. I'm sure Sam and Dean would be happy to deal with the Novaks, right boys?"

Sam nodded at his mother, and Dean could feel his excitement bubbling. He looked to his brother and saw a dark glint in his eye. The two of them together were unstoppable. 

"Anything for you, mother," Dean said, and he basked in her pride.

"Wonderful," John said, clapping his hands together, dispelling the tension surrounding the table, and causing Bela to sink back into her seat as her concerns were dismissed. "Now, let's eat before the food goes cold."

The rest of the evening dissolved into easy conversation amongst the members of the meeting. Sam laughed wildly at Bobby's account of a man who he had once held over a woodchipper for his disrespect, even though he had told the story a hundred times. Mary and John spoke quietly with Jessica about her parents and how thrilled they were that her contacts on Broadway would benefit the Winchester dynasty. Dean occupied himself by kicking Jo under the table and watching her face go from mildly irritated to genuinely annoyed as she tried to maintain a discussion with her mother about liquor importing.

When the food and wine had been consumed, John stood again and waited patiently for the conversations to cease. "Thank you all for joining us this evening." He spoke warmly to everyone. "I trust to see you all again next month." A chorus of murmured agreement rippled through those assembled. John raised his glass, and everyone else followed suit. "To the family." He toasted and drained the remaining wine from his glass.

The sound of chairs scraping back from the table filled the small dining room as the Winchesters and their associates made to leave. They passed the other patrons, enjoying their meals and trying obviously not to stare as the finely dressed men and women filed out the front door, thanking Cain with handshakes and smiles as they left.

Dean stepped into the street and stretched, breathing the exhaust soaked air deeply into his lungs and once again being reminded of just how much he loved this city. A large hand dropped heavily onto his shoulder, and he turned to find his gargantuan little brother towering next to him.

"You wanna come over for a beer?" Sam asked casually.

"Nah, man, I was thinking about heading over to Lee's," Dean said. His head was foggy from the wine, and he needed some real liquor to bring his senses back.

Sam scowled. "You know, Dad doesn't like you going out without protection."

"Always keep a condom in my wallet, Sammy." Dean winked, and Sam rolled his eyes dramatically.

"That's not what I mean." He said. "If Bela is right and the Novaks are looking to start a war, none of us should be going anywhere alone."

"Oh, is Sam freaking Winchester scared of a few Jersey boys?" Dean snarked at his brother, punching him in the arm playfully. "I'll be fine. Besides, it's Lee's bar. I'm basically royalty there."

Jessica appeared at Sam's side and snaked her arm around his waist. She really was beautiful, far too good for his brother. Dean sometimes wished he had met her first, but he shook the thoughts from his mind. Sam was happy with Jess, and that's what he deserved.

"Your parents invited us over to look over the blueprints of the new hotel, honey." She said. "Dean, will you be joining us?"

"Not tonight, sweetheart, but hey, tell 'em to put one of those fancy water features in like they've got in Vegas," Dean replied sarcastically.

Jess smiled at him. "You ready, Sam?"

"Uh, yeah, one second. Why don't you go ahead with Mom and Dad? I'll meet you at the car." Sam said. He rubbed his hand across her shoulders and leaned down to kiss her sweetly. Jess cast one more smile at Dean before turning back down the sidewalk to where Mary and John stood waiting. 

"What's up, Sammy?" Dean asked. He knew there was a reason his brother was holding him back.

Sam stepped closer to Dean and quickly looked over his shoulder before shoving his hand into his pocket and producing a small black velvet box. "I was going to wait until tomorrow, but I can't help myself." He said, opening the box. Inside was a beautiful diamond engagement ring. The center stone was massive and cut into the shape of a teardrop. On each side were two smaller diamonds, surrounded by a cluster of sparkling rubies. "I'm gonna ask Jess to marry me."

Dean laughed out loud. "Holy shit, Sam!" He blurted out loudly and pulled his brother into a hug.

"Shhh!" Sam warned. "Keep your voice down! I don't even know if she'll say yes."

Dean scoffed. "Of course she'll say yes! You two have been together, what, forever?" He grinned. "Although, if she does say no, you can tell her I'm available."

Sam smacked him around the head, and Dean laughed. "Alright, have fun at Lee's. Call Benny if there's any trouble."

Dean waved over Sam's shoulder at John, Mary, and Jess, and gave his brother a nod before turning and heading down the dark sidewalk in the direction of Lee Webb's bar.

Swayze's was more than a few blocks from Cain's place, but Dean didn't mind the walk. He'd left his car at home after visiting Gordon this afternoon, and he enjoyed the refreshing night air against his face. The downtown lights glared into the sky through the ever-present smog rising from the city, and Dean hummed a little to himself as he walked. This was his city. The Winchesters owned these streets. He knew one day, the empire his mother and father had built would fall to him and Sam to manage, but that time was a long way off. John would never relinquish control of the family assets to his sons while he still drew breath, and without any heirs of their own to ensure the continuation of the dynasty, that was even less likely.

Dean smiled to himself, thinking of the ring currently sitting in Sam's pocket. Jess would be an excellent addition to the family. Her parents were both high profile talent agents on Broadway with a lot of influence there and in Hollywood. There had never been a reason for the Winchesters to get into theatre, but he knew they wouldn't turn down the opportunity if Jess said yes to Sam tonight. His smile faltered slightly. It had been a long time since Dean had been as happy as Sam was now. His last relationship had been with Lisa Braeden, and that had only lasted a few months. She had a young son, Ben, who Dean still saw on occasion, but he had left when things had started to get really serious. He wasn't going to drag someone else's kid into this mafioso life. It wasn't his place.

The truth was, Dean didn't even know if he wanted kids. He'd thought about it, sure, and his mother had been pressuring him since his mid-twenties to find a nice girl to make babies with, but Dean liked his hang-up free lifestyle. He was happy to carry out orders for his father, help the family, and maybe hustle a few out of town suckers at pool when the mood struck him. Sam was business-minded, and Dean was more than happy to allow his not-so-little little brother to take over for their father when the time came.

Dean had been so deep in his own head that he barely registered when he had arrived at Lee's. He sat down on a barstool and scanned around the room. Dean sighed contentedly. As he had expected, the bar was devoid of anyone immediately recognizable save for Lee himself.

Dean rapped his knuckles on the bar top to get Lee's attention. "Who do I gotta gank to get a drink around here, hey buddy?" He said as Lee tossed the towel he had been using to clean a pint glass over his shoulder and turned to Dean. His expression changed from annoyed to ecstatic when he registered who was speaking.

"Dean freaking Winchester." Lee drawled. "It's been a while. You too good to come see me anymore?"

Dean grinned. "Never too good for you, Lee."

"What'll it be? On the house." Lee spread his arms, gesturing at the impressive selection of alcohol arranged along the wall behind him.

"Whiskey. Neat." Dean replied. Lee nodded approvingly, selecting a bottle from the top shelf and pouring a heavy-handed three ounces into a glass. He slid it across the bar to Dean, and he took a sip, letting the liquid burn deliciously in his throat and warm him from the inside out.

"That's good stuff." Dean smiled as a low rasp crept into his voice.

"Only the best for you." Lee matched his tone. "So, what brings you out tonight?"

"Dinner with the family," Dean replied noncommittally.

"Yeah, you always did hate those." Lee whipped the towel off his shoulder and picked up another glass, wiping the water from around the rim. "Anything exciting?"

"No, just business as usual. Bela is being a bitch, Bobby's still telling the same stories he has for the past 20 years..." He paused before taking another sip of his drink. "Oh, and uh, Sammy's gonna ask Jess to marry him."

"No shit!" Lee said, his eyebrows rising in mild surprise. "I'd say that's pretty exciting."

"Yeah, it's been a long time coming." Dean chuckled into his glass. "Never seen anybody as happy as those two. Kind of a miracle she hasn't killed him yet with what a pain in the ass he can be."

"Ah, you're only saying that cuz he's your brother." Lee laughed.

"Yeah, well, brother or not, he's still a giant pain." Dean downed the rest of his drink and tapped the rim for a refill. Lee shook his head but complied. 

"You feeling a little jealous there, buddy?" Lee smiled devilishly at him as he set the bottle down on the bar top.

Dean chuckled darkly. "Nothing to be jealous of. I've got my life, my health, my family," he grinned at Lee over the rim of his glass. "And a buddy with a bar. What more could a guy need?"

Lee shook his head but said nothing. Dean appreciated the silence that fell immensely.

The sudden clatter of a barstool hitting the floor drew Dean's attention to the opposite end of the bar. Two men stood chest to chest, shoving each other back and forth.

"What the fuck is your problem, man?!" One of them exclaimed.

"What's my problem? What the hell is your problem?!" The other responded, punctuating his words with a shove to the man's shoulders.

"Hey!" Lee shouted. "Take it outside, boys."

"Yeah, some of us just wanna drink in peace," Dean said.

"What the fuck did you just say?" One of the men said to Dean. Having found a common enemy in him, the two men turned towards Dean's seat and advanced. He drew in a breath, immediately regretting his decision to speak up. They were both much larger than him by a wide margin, and Dean couldn't help but think to himself ruefully that maybe Sam was right about needing protection.

As he balled his fists, ready to start swinging, he felt someone step into the space at his side.

"I believe both of these fine gentlemen just politely told you inbred walnuts to get lost." The voice that spoke was low and gravelly, and Dean felt his stomach flip a little at the sound of it. He turned his head to identify the stranger and was met by a tan trenchcoat.

His eyes travelled upwards to the man's face, and Dean felt his stomach do another small flip. A strong jawline covered in light stubble, slightly chapped pink lips, and tousled black hair were Dean's first indications that the man suddenly standing next to him was unfamiliar. When the man cocked his head slightly, Dean caught his eye and felt his breath hitch in his chest. Framed by thick, dark eyelashes were a pair of icy blue eyes that Dean very quickly found himself staring at. He looked away as soon as he realized because, as much as he would have loved to stare, the two aggressively drunk men in front of him posed a much more immediate problem.

Returning his attention to them, Dean rose from his seat and drained the remaining liquid from his glass, vaguely registering that Lee had also rounded the bar and was standing behind him.

"Well, fellas. Looks like it's two against three." Dean said, gesturing at Lee and the stranger. "Not that I don't like those odds being in my favour and all, but I'll give you a chance to walk away before this gets too outta hand." He heard Lee crack his knuckles and grinned. There was no one in this world Dean would rather have in his corner for a fight than Lee Webb, except maybe Sam.

The two men in front of him hesitated slightly before one of them let out a yell and charged towards Dean.

He reacted in an instant, ducking below the man's outstretched arms and coming up under his knees to flip him over his back towards Lee. He heard the man hit the ground with a thud as Lee reached down and heaved him back up into the edge of the bar. Dean turned just in time to see the other man following his partner towards him, arms reaching out like some great ape. He didn't have the forewarning or space to execute the same move, and so he simply ducked out of reach. As the man's arms closed above his head, he heard the unmistakable sound of a fist colliding with a nose as the cartilage and bone crunched under the force. Glancing to his right, he saw the trenchcoated stranger land a blow directly into the second assailant's face and smiled to himself. _Not bad,_ he thought.

As the ape staggered back, clutching his now broken nose, blood streaming down between his fingers, Dean stood up and grabbed the man by his shirt. Together, he and Lee shoved the two towards the bar's door and unceremoniously tossed them into the street.

"Don't let me catch you goons in here again," Lee shouted as they took off quickly down the alley.

Dean watched them go and shook his head ruefully. Even at Lee's, trouble managed to find him. He looked to his friend and put a hand on his shoulder, squeezing lightly. "You okay?"

"Yeah, yeah, I'm fine," Lee said, brushing him off. "Guys like that aren't a problem. You and I both know I've fought worse."

Dean laughed. "Ain't that the truth." They turned to go back inside, and Dean spied the mysterious stranger as he picked up a stool that had fallen over in the scuffle, cradling his right hand against his chest.

"Hey," Dean called out to him. The man looked up at Dean, and he was pierced by the full intensity of his stare. Those blue eyes, which before had been icy and cold with adrenaline, were now pools of deep ocean blue, and Dean once again felt himself beginning to drown in them. He cleared his throat, trying to get rid of the lump that was quickly forming there. "Um, thanks. For that. You, uh, you didn't have to get involved. Lee and I could have handled it."

_Way to sound ungrateful, Winchester_ , he kicked himself internally.

The stranger cocked his head to the side as he stared at Dean, his eyebrows knitted together in the most perplexing stare Dean had ever seen. Lee walked up next to him. "Lemme get you some ice for your hand. If that dude's skull is as thick as it looked, you're probably hurting pretty bad." He walked behind the bar and began filling a small bag with ice. "Oh, and your next drink is on me. Dean may not know how to actually say thank you but, we aren't all as uncivilized."

Dean felt the heat rising in his cheeks as he sat back in his seat, and Lee refilled his glass, adding a second one for their new friend. "Thank you." The man said, taking the bag of ice and placing it over his knuckles. He took a small sip of his drink and set it back on the bar top.

Dean shook himself and realized the man was still staring at him, and being under his scrutinizing eyes made Dean fidget uncomfortably. He cleared his throat again. "So, uh, you got a name?" He asked. Then, because Dean was not one to relinquish the upper hand, he plastered on his charming Winchester smile and said, "Or am I just supposed to call you handsome?"

A small smile lifted the corners of the man's lips as he extended his uninjured hand for Dean to shake.

"Novak." He said, and Dean felt the colour immediately drain from his face.

"My name is Castiel Novak."


	2. Drinks

**Notes for the Chapter:**

> Thank you to everyone who read and enjoyed the last chapter. Your comments were all so kind and meant so much to me. I know I said chapter 2 would be up on Tuesday, but I couldn't wait anymore. As always, if you wanna chat, send me a message on [tumblr.](https://www.tumblr.com/blog/bktynes-writes)

Dean's mouth had gone dry. He sat, frozen, hand clasped firmly in the grip of the man in front of him. He was dimly aware of the fact that he had taken far to long to respond, and the look Castiel was giving him now made him even more painfully aware of the knot forming in his stomach.

_Novak_. The name rang in his ears. He composed himself and managed to shake the man's hand before withdrawing his own and lifting his glass. 

"Novak, huh? What is that, Serbian?" He grinned at the surprised look that crossed the face of the other man.

"Yes, actually." He turned back to face the bar. "Most people don't get that the first try."

Dean chanced a glance at him from the corner of his eye and caught the small smile still tugging at the corner of his lips. Something in Dean's chest tightened as he wondered what it would be like to see  
him smile in earnest.

"So, Castiel, do you make a habit of jumping into random people's bar fights?" Dean asked. He motioned to Lee for another round. The alcohol in his veins made him less aware that he was sitting with a potential rival and more aware of how attractive he found the man.

"No, I can't say that I do," Castiel replied. "But I'm new in town. And I like this bar. I would rather it not be sullied by unsavoury company." He thanked Lee with a nod as he placed down two bottles of beer on the bar.

"Well, Dean here is about the most 'unsavoury' as it usually gets in here, and you seem to have made his acquaintance rather nicely." Lee provided with a smirk.

"Dean," Castiel said to no one in particular. It was like he was testing the name, rolling it around on his tongue to see how it felt, and when he let it loose from behind is lips in that low growl of a voice, Dean felt his knees wobble, making him very thankful for the stool under him.

"Right, yeah. Dean Smith," He introduced himself, and he didn't miss the look from Lee who, mercifully, did not comment at his use of a pseudonym. "Sales representative with Sandover Enterprises." He smiled.

"Sandover?" Castiel questioned. "The steel distributor?"

"The very one," Dean replied, raising his beer to Lee and giving him a look that he hoped conveyed the importance of his silence. It must have worked because Lee turned and busied himself cutting limes on the back bar.

"I see." Said Castiel. "Tell me, Dean, can I often expect to have to jump in and save you from brutes prowling alleyways and backwater establishments? No offence." He added to Lee, who raised his hands in surrender and continued to obviously ignore their conversation.

Dean chuckled. "No, I'm usually good on my own, Cas. It's just been a long day."

Castiel's lips twitched at the use of the nickname. "Ah. I understand. The last few weeks have been...exhausting."

"Oh yeah?" Dean looked the man up and down, letting his eyes linger slightly on his broad shoulders, his throat where his adam's apple bobbed as he swallowed, and back to his impossibly blue eyes. "You don't look like a labourer. And I'm guessing this whole tax accountant thing you've got going isn't the case either from the way you swing a punch. What do you do?" He felt like he was in grade school trying to make friends again, asking what their favourite colour was.

"My family..." Castiel began, pausing and looking down at his drink. "Let's just say we've got varied interests." He smiled slyly at Dean, who was suddenly very aware of how his hands were itching to reach out and thread themselves through Castiel's hair. He kept them clasped tightly around the cold glass of his beer bottle instead.

"Well, maybe it's a good thing I ran into you then, Cas," Dean drawled. He let his tongue dart out quickly to wet his lips and didn't miss the way Castiel's eyes flicked down at the movement. "I've got some 'varied interests' of my own." 

Dean could see the man's pupils dilate over the bottle that hung at his mouth. There was a distinct red tinge to his cheeks as his eyes flitted across Dean's face, from his lips to his eyes to his throat, back to his lips. Dean pulled his lower lip between his teeth and smiled at the nearly inaudible gasp that escaped the other man.

Dean heard Lee cough, fake and dramatic, behind him. He grimaced as the trance Castiel's eyes held over him was broken. Cas shook himself and turned his face from Dean to peer sheepishly at Lee, who was now smirking at both of them.

"Well, Mr. Smith, thank you for this...eventful evening. When I say the pleasure was mine, I mean it most sincerely." He took one last long swig from his beer and clambered off of his seat. "Perhaps if I'm lucky, I'll get the chance to see you again." He turned on his heel, trenchcoat billowing behind him as the breeze from the door caught it. Then he was gone.

"Dean Smith?" Lee chided. "Really?"

Dean didn't realize he had turned to watch him leave until he heard Lee speak. He spun around to see a knowing smirk plastered across his face and rolled his eyes.

"What?" Dean scowled, taking a few more gulps from his beer.

"Nothing, man, nothing..." Lee chuckled. "Just the next time you eye fuck a dude at the bar, you should probably have the decency to give him your real name. Maybe your number?"

"Shut up." Dean groaned. "I just heard about the Novaks tonight at dinner, okay? Bela says they're trying to start a war in her district, and Sam and I are supposed to 'deal' with them." He pushed the heels of his hands into his eyes until stars popped behind them. "Why did it have to be Novak..." He said quietly.

Lee roared with laughter. "Because you, Winchester, invite trouble wherever you go, and I have seen that look on your face before."

Dean flipped Lee the bird and reached over to take Castiel's abandoned beer bottle. "Yeah? What look is that?"

"You think he's cute, and you wanna feed him shots until he's drunk enough to let you blow him behind the dumpsters at Antoni's on 64th St." Lee raised an eyebrow as Dean choked on his mouthful of beer.

"That is...oddly specific," Dean said when he recovered.

"Only because it's the same way you used to look at me." Lee shrugged and turned back to his limes as Dean glowered at him. "And that's _specifically_ what happened with us."

"That was thirteen years ago, Lee," Dean said, his voice dropping. "Things are different now."

"I know, I know. Things change, people change even more," Lee glanced over his shoulder, the same shit-eating smirk as before stuck on his face, but this time it didn't quite reach his eyes, "you've always been a hopeless romantic Dean, no matter how much you hate to admit it. And I like to think, after all this time, I know you pretty well, sometimes even better than you know yourself."

Dean looked away as Lee made a few more drinks for some of the other patrons. He couldn't bring himself to look him in the eyes. He was right; Dean _did_ find Castiel attractive.

It was getting late, and as more people rolled in off the street to escape the rapidly cooling night, Lee became too busy to chat with Dean any longer. He finished the two bottles of beer in front of him, bid Lee a quick farewell with a promise to come back again soon, and walked out into the night.

He was rather tipsy now, and the alcohol sloshed warmly in his stomach as he walked back through the city towards downtown. He wasn't ready to go home yet, but the conversation with Lee had left him feeling less than willing to engage in meaningful human interaction, and he knew there was a strip club a few blocks away that might offer just the distraction he needed.

He shoved his hands deep into his pockets and pulled out a crushed pack of menthol cigarettes. Dean didn't often smoke, but the alcohol combined with the thoughts in his head had him craving the sweet sting of nicotine. He stopped on the corner and lit one of the white paper tubes, hissing on the inhale as the minty smoke filled his lungs.

What did Lee know? So what if he thought the dark-haired, blue-eyed man in the trenchcoat was cute? He was a Novak, and if Bela was to be trusted - which he quickly reminded himself was questionable - that made him the enemy. Still...Dean found himself thinking more and more explicitly about Castiel as he continued to walk.

Would his pupils blow wide with desire and blackout that gorgeous blue if Dean touched him in just the right way? What would his already messy hair look like after having had fingers run through it a few times? How would Dean's name sound, groaned and gasped, in that rough voice, made deeper by lust? What would those chapped, pink lips look like slick with spit, wrapped around his - 

"Hey! Watch it, buddy!" Shouted a voice as Dean's shoulder bumped into another man on the sidewalk. "Fuckin' drunk..."

Dean couldn't even be bothered to respond to the man he had walked into. He really had been deep in his thoughts. Looking up, he realized his feet had once again carried him unconsciously to his destination, and he praised his knowledge of the city for allowing him to lose himself without getting lost.

Rowena's club was one of Dean's favourite places - second only to his car - and the buzzing neon sign above the door was music to his ears. Emerald green cursive spelled out "Eden" and turned into a snake coiled around a deep red apple missing a single bite. Dean delighted in the sacrilegious nature of the name. Given the activities that went on behind its doors, it suited the place. The knowledge that Rowena had chosen "Eden" to be intentionally heretical brought a smile to his face; even in Catholic school, Dean had never had much respect for the bible.

He cut the line with a curt nod to the bouncer and walked through the doors into the dimly lit club. Dean felt the tension of the evening evaporate from his limbs as soon as the pervading scent of cherries and tequila washed over him. The black brick walls and tables draped in blood-red velvet made the room feel smaller than it really was. It was hardly past midnight, and yet every table was full of men, mostly suits from the business district here to pretend their sexless marriages weren't failing. Dean snorted. Sam could have his apple-pie life with Jess; at least Dean would never end up like these poor schmucks.

Out of habit, he scanned the crowd and saw a few familiar faces, but thankfully no sparkling blue eyes and no trenchcoats in sight. The brightest source of light came from the rotating floodlights on the main stage. Dean supposed that keeping everything in shadow allowed people to feel more comfortable here. After all, a strip club may be fine and well, but when the money changed hands and gentlemen were lead to back rooms by beautiful ladies, it was best that no one knew each other's names in the morning.

A young woman in her early twenties gyrated and slowly removed her clothes on the main stage to the beat of the rock music blaring through the speakers. Dean couldn't help but watch her as she moved, dark hair falling over pale skin as she thrust her hips sinfully against the stage. Dean once again found his mind wandering, and he forced himself to engage the bartender in conversation as a means of distracting himself.

"Hey there, handsome," She said to him as he sidled up to the bar. "What's your poison?"

Dean noticed the way she leaned enticingly on the bar as she spoke, shoulders back, chest out in invitation for him to stare. He let his gaze linger for a moment before returning her suggestive smirk.

"Just a water for now, darlin'," he said. He could feel the whiskey from Lee's slowly soaking into his brain, clouding his judgement.

"Aw, you're no fun," the bartender pouted, placing a glass in front of him and filling it with water from the gun attached to the bar. "What, are you some kinda teetotaler or something?"

"Nah, nothing like that," Dean chuckled. "Just had a few already and wouldn't wanna forget your pretty face."

The bartender smiled coyly and extended her hand for him to shake. "Pamela." She said.

"Dean." He replied, taking her hand delicately in his own. "Do you just mix drinks around here, or can I look forward to seeing you on the stage later?"

She laughed. "I dabble. But tonight's not my night. I get off around three though, and uh, well, if you're still around, maybe you can too." She winked at him before being called down the bar. Dean watched her walk away, the sway of her hips capturing his attention.

"Well, well, well..." Dean heard the unmistakable accent drawl from behind him. "A Winchester. Alone in my club. To what do I owe the honour?"

Rowena was a tiny woman who had come from Scotland and made quite the name for herself in America's lucrative sex industry. She ran a tight ship with her girls, who did everything from stripping to pornography to escort work, and, in the case of Ruby and a few others, the occasional special favour for the Winchesters. No man controlled Rowena or her girls, and if anyone ended up on the wrong side of the devious little redhead, they were likely to find themselves in a sealed box at the bottom of the river.

"Rowena," Dean stated simply, rotating his chair to face her as she stepped closer to him. Her red gown caught what little light the club offered and shimmered. 

"I expected I'd be getting a visit from you boys soon." She sighed heavily and waved to Pamela, who nodded and brought her a martini glass of something pink and fruity-looking. "I was hoping it would be Samuel coming to call, but I guess you'll do."

"Oh yeah? Why's that?" Dean asked, sitting up straighter in his seat.

"Well, I suppose it's his well-muscled arms, his gorgeous hair, his tall, strong physique..." She mused, sipping her drink with a smirk.

"No, not that, Rowena, and ew," Dean cringed. "Why were you expecting us?

"Perhaps because of those Novak boys that Miss Talbot had Ruby go looking into." Her face darkened. "I don't know what she was thinking, but that poor girl came back beat half to death. She was a good dancer, always made a lot of money on her nights..."

"Where is she now?" Dean asked. "I wanna know what happened."

"Ah, well, we agreed it was probably for the best if Ruby took some time out of town." Rowena swirled the liquid in her glass and looked away from Dean to the stage. "I have other dancers that can fill her slot for the time being."

"Where is she?" Dean asked again, an edge to his voice that made Rowena glare.

"Not here, Winchester. And if you think for a moment that I'm so disloyal to my girls that I would tell you where she's gone, then you are sorely mistaken." She defended. Dean didn't push the issue. Her mind was made up, and there was no amount of bargaining or coercion that would change it.

"Alright, so why don't you tell me what happened then?" He directed. Rowena pursed her lips into a thin line. She was the only person Dean had ever met who could rival him and his brother for stubbornness.

Rowena sighed. "Oh, why not. The more, the merrier, I suppose." She gestured to a table next to the bar where an attractive young man stood guard, keeping the table open. She waved at Pamela for more drinks and slid into the booth's bench, touching the young man's arm gently as she did. When they were seated comfortably and had been presented with a fresh round of drinks - Pamela had ignored Dean's continued request for water and had brought him another glass of whiskey - Rowena continued. "What do you want to know?"

Dean wasted no time. "The Novaks." He said. "Who are they?"

"I can't say that I know too much, honestly." She purred. "But after the incident with Ruby, I did a little research. It would seem that the father, Chuck, had a wife years ago, Naomi, who was killed in some kind of gang war. He became obsessed with revenge and took over a good chunk of Newark, eliminating the gangs, building the communities, doing all sorts of goodwill charity work, all with funds gathered through several nefarious means." 

"What sort of means?" Dean asked again.

She sipped her drink slowly before she continued. "Standard fare. Murder for hire, arms dealing, the occasional theft. If I had to guess, that'd be what made him target Bela in the first place. I don't know if you've noticed, but that woman can be a wee bit hard to handle. Not the type to make many friends." Dean snorted. He had no arguments there. 

"Now, Chuck and Naomi had four sons before she passed. Apparently, everyone is a bloody Catholic because they named them all after archangels, the poor boys. Chuck started sort of 'collecting' street kids who had lost their families to the gang wars. He took them in, made them a home, and built his own family, not out of associates and partners like you lot, but an actual family of brothers and sisters." She pushed her glass away and leaned forward into Dean, dropping her voice barely above a whisper. Dean had to move even closer to catch her words as the music from the club's speakers continued to fill his senses. "They are ruthless. Especially the four oldest brothers. They will fight and kill and bleed for their family, and they will smile while they're doing it. You think you and Samuel are close? You've got nothing on these boys."

Dean swallowed hard. Rowena wasn't one to exaggerate. If she said the Novaks were dangerous, he had no reason not to believe her. "How much of a threat are they?" He asked bluntly.

"Well, they certainly aren't a problem you should ignore." She smirked. "But, I do have a feeling that some of that Winchester charm could come in handy." She reached out and tapped Dean lightly on the tip of his nose. 

"Thanks, Rowena," Dean said, slipping out of the booth. "And if you see or hear anything else..."

"I'll be sure to call you, quick as a whip." She said sarcastically. He nodded and headed towards the door. Pamela's earlier proposition rang in his ears, and, as much as he wished he could stay and accept, his gut was telling him to return home and relay the information from Rowena to his brother.

He staggered out into the alley again and rubbed his hands together to stave off the rapidly cooling September night. He thought about calling Benny for a ride. The Winchester bodyguard could always be relied upon to answer his phone at any hour and never say no to Dean. He pulled his phone out of his pocket and frowned. The screen displayed several missed calls from Sam and a few from his mother. He grinned widely. They were probably calling him to chastise him for not being present for Sam's proposal. 

Quickly tapping open the screen, he dialled his brother's number. It only rang once before Sam's voice came through the other end.

"Dean?"

"Hey, Sammy!" Dean beamed into the phone, staggering a little on the uneven sidewalk. "So? Did she say yes? Is my baby brother getting married?"

"Yeah, Dean, she did. Where are you?" Sam huffed into the phone.

"Out," Dean stated. "Celebrating on your behalf." 

"Are-are you drunk?" Sam stammered into the phone.

"I mean, pshhh, maybe? A bit?" Dean smiled. He was feeling great. Who cared about that pretty-eyed guy in the trenchcoat at Lee's? Dean didn't care. And he didn't care that he didn't care. "Listen, I talked to Rowena and - " Sam cut him off before he could finish his sentence.

"Jesus Christ, Dean!" Sam yelled into the phone, and Dean immediately began to lose whatever happy buzz he had gained through the night. Sam never yelled at him. "It is 2am, and I've been trying to call you for HOURS! I even called Lee's, but he said you left before midnight, and now you're wasted downtown by yourself and I just..." There was a long pause on the other end of the line. Dean could hear Sam taking deep breaths to calm down.

"Hey, hey, Sammy, listen, I'm okay." He tried desperately to soothe his brother's worries. The panic in Sam's tone had sobered him, and he transformed immediately into Big Brother. His primary focus was back on protecting his little brother, making sure he wasn't afraid. "Everything is fine. I'm not wasted, just a little buzzed. I'm gonna call Benny for a ride and head back to my place. I'll text you when I'm home and call you in the morning, okay?"

"No, Dean," Sam said weakly into the phone, "it's not okay."

Any remaining happiness Dean had from the alcohol was extinguished. His feet stopped moving, and his own voice seemed distant as he spoke. "What's wrong, Sammy? What happened?"

Sam sounded like he was speaking through a tub of water. "It's Dad. You need to get home."

**Notes for the Chapter:**

> Kudos are so appreciated, and comments make me smile. Thank you again for reading and, if you have the time, why not pop over to my [tumblr](https://www.tumblr.com/blog/bktynes-writes), reblog this post, maybe even give a cheeky follow ;)


	3. The Father

**Notes for the Chapter:**

> Hello, hello, friends! Happy Canadian Thanksgiving! I'm sorry this chapter took a little longer to post than usual, but I wanted to give people some time after "Last Holiday" to appreciate all the other wonderful content that came out surrounding that. I hope you all have a wonderful week and, as always, I'd love to hear your thoughts!
> 
> Come hang out on [Tumblr](https://www.tumblr.com/blog/bktynes-writes) with me!

The car ride from Rowena's club to the Winchester estate was silent and even more sobering for Dean than his phonecall with Sam had been. Benny had, of course, answered his call and driven to pick him up without question the moment Dean had said he needed a ride. Now he found himself sitting in the backseat of Benny's SUV staring at the palms of his hands, trying to compose his emotions for what he would be walking into. He hadn't let Sam explain over the phone, just said he was on his way and hung up, immediately dialling Benny's number.

His emotions ranged from fear to rage, and he was doing his best to school himself into some manner of togetherness before reaching his parent's home but was failing miserably. He caught Benny glance at him in the rearview mirror.

"You wanna tell me what's wrong, brother?" Benny asked, his cajun accent filling the cab of the vehicle.

"No." Dean snapped. There was nothing to talk about until he knew what had happened to his father.

Benny sighed. "You can't run from everything, Dean-o."

"Just drive, Benny. I'm not in the mood." Dean said. 

"Fine, fine," Benny shook his head and turned his eyes back to the road. "But you should talk to someone. Spending your nights in the company of Rowena's harlots ain't gonna make the mornings feel any less cold."

Dean shot him a look over the back of the seats, and Benny focussed his eyes back on the road. He felt an immediate pang of guilt. Benny didn't know that he wasn't just pining over some woman with a fake name and even faker tits. He couldn't.

Dean sighed. "It isn't that, man." He curled his arms around himself. "It's dad. Something's wrong."

Benny's eyes snapped up. "John? What happened?"

"I dunno. Sam just called and said I needed to get home." He thumbed at the screen of his phone idly. "Could be anything."

"Well, shit, brother, if I'd've known this wasn't just a drunk Dean episode, I woulda been driving faster," Benny said.

He took a hard left, and the Winchester's estate loomed into view. The old house's stonework visage was enveloped in dark coiling ivy, and the yellow light from the windows glinted like eyes in a dark, expressionless face. The granite front steps led to grand wooden doors, intricately decorated with a relief carving of David's battle with Goliath. Dean scowled at the trees that adorned the side of the drive, casting their looming shadows through the back window of the SUV. They stood like sentinels, stoic and unyielding, daring any who passed to try and shake the Winchester's roots.

The tires crunched on the driveway's gravel as Benny pulled the car around the ornate fountain that sat at the base of the stairs. Dean unbuckled his seatbelt and threw open the door when it came to a stop.

"Thanks for the lift." He said over his shoulder to Benny as he slammed the door.

Benny rolled down the passenger window. "Any time, brother. You want me to wait for you?"

"No, it's fine. Thanks though. Just maybe don't go home yet? No sense keeping the wife awake if I need to call you again in a few hours." Dean said and forced a smile.

"Sounds like a plan." Benny looked at him with sad eyes and gave a final nod before turning back up the drive.

Dean watched the taillights recede into the inky blackness, the fountain's cascading water like white noise to his rushing brain. He quickly walked the few steps up the stairs and heaved open the front doors, light spilling out into the night, and stepped inside.

The front room was just as it had always been, a monument to excess with gilded fixtures and chandeliers that hung like diamonds from the rafters. Dean closed the doors behind him and called out to the depths of the house.

"Mom? Sam?" It was late, and, under normal circumstances, he would never have disturbed the silence.

"Dean." Sam appeared at the top of the grand staircase. "Benny got you here fast." A deep crease decorated his forehead, and dark circles hung under his eyes. His long hair, usually well kept, was sticking up on one side as though he had been running his hand through it for hours.

"Yeah, I told him you were pissed; what the hell is going on?" He climbed the stairs and followed his brother through the winding halls of the second floor, their heavy footsteps muted by the plush carpet underfoot.

"We were all sitting around after I proposed to Jess..." Sam kept his eyes forward, unblinking. "Mom and Dad were so happy. Mom, she couldn't stop talking about colour schemes and napkin patterns. Dad and I were going down to the cellar to get another bottle of wine. He insisted. Said, 'it's not every day your son gets engaged.'" He laughed darkly as they reached the master bedroom, and Sam rested his hand on the doorknob. Dean stopped in his tracks behind him. "He just...dropped, Dean. I didn't even have time to catch him before he hit the floor." Sam looked up, and Dean saw tears brimming in his already red-rimmed eyes. He opened the door to the bedroom, and they both stepped inside.

John lay on the bed, tubes and machines that had never before occupied the room's space hooked to his arms. A plastic mask secured over his face pumped oxygen to his lungs as the rhythmic beep of the heart monitor ticked away the seconds of his life. Jess sat in a chair next to the bed, her arm wrapped around Mary's slumped shoulders. They rose as the brothers entered, and Jess immediately threw her arms around Sam's waist, burying her head in his chest as he stroked her hair tenderly. Dean rushed to his father's side.

"Dad..." He choked out, taking John's hand in his own and gently squeezing it, as though he expected his father to wake from his touch alone. He turned to his mother. "What happened?" He demanded harshly.

"Heart attack." Said a smooth voice from the other side of the bed. Dean snapped his head around and spotted a woman examining one of the machines that snaked tendrils of fluid into his father's lifeless form. "Your father's in a coma as a result of cardiac arrest induced hypoxia." She scribbled something on her clipboard. Her sterile white coat stood in stark contrast to the umber glow of her complexion, the seriousness of her face softened by the low light of the room.

"In English." Dean snapped at her.

The woman fixed him with a stare that made Dean shrink back slightly. Her coal-black mane of hair seemed to crackle with intensity as she appraised him. "His brain couldn't breathe." She replied bluntly.

"Dean, this is Dr. Berry," Mary said gently as the two continued to stare at each other, neither willing to give the other the satisfaction of looking away first. "She agreed to treat your father at home instead of the hospital."

"Call me Billie." Said the woman, finally relinquishing victory of the staring contest to Dean as another machine beeped insistently for her attention. "I wouldn't normally recommend allowing a patient in his condition to remain at home, but what a Winchester wants, a Winchester gets."

"Is he gonna be okay?" Dean growled.

"Hard to say," Billie responded. "The cardiac event has severely weakened his heart, but it's the brain function I'm worried about."

"Meaning?" Dean didn't like this woman. She challenged him, and in a situation where he already had no control, he didn't appreciate the condescension in her tone.

Billie sighed as she placed her clipboard on top of the machine. "He'll probably survive the heart attack, but the fact that his brain was without oxygen for an extended period may mean he doesn't wake up. We'll take it day by day; most patients do recover eventually, but as I always say, pray for the best, prepare for the worst."

"Yeah, well, I'm not much of the praying type." Dean returned his gaze to his father's face, peaceful as he'd ever seen it, and fought to hold back a single tear that threatened to fall.

"Somehow, that doesn't surprise me." Said Billie. Dean glowered at her. She turned to address his mother. "I have to return to the hospital. I'll send a nurse by in a few hours to check on him. If any of these machines readings change from what I've noted here, call me immediately. You have my number." Mary nodded, and Billie swept out of the room, shutting the door behind her without so much as a glance at Sam or Dean.

Dean's stroked the knuckles of his father's hand with his thumb. _What kind of son are you?_ He thought to himself. _Out drinking in whore houses, flirting with the enemy? He would be so ashamed of you. Sam is the only good Winchester boy. You don't matter. He'd beat your ass if he knew what you were doing tonight. Remember when he found you and Lee? Imagine if he knew what you were thinking about doing with Castiel..._ Dean shook the thoughts violently from his head.

"We need to keep this quiet." Dean heard his mother say distantly. "And we'll need to move up the wedding. I can pull something together in two weeks. Jess, call your parents and see what the earliest they can fly out is. Money won't be an issue." Dean whipped around in his seat, rage burning in his chest.

"Really?!" He snapped at his mother and brother. They stood huddled by the door, their expressions resolute, Sam still cradling Jessica in his arms, rubbing her shoulder firmly as she sobbed lightly into his chest. "Dad is a freaking vegetable, and you're worried about a **wedding**?!" He stood briskly and made to storm out of the room, but Mary stopped him with a firm hand placed on his chest.

"Dean," she said, looking him sternly in the eye. "We need to show that we aren't weak. This couldn't have come at a worse time. With Bela's news about the Novaks, a wedding would prove to our enemies that the Winchester bloodline, the Family, is still strong. Your father is the reason we aren't wallowing in the gutter like rats. Without him, those who would seek to destroy us will move against our empire with the forces of Hell behind them." She dropped her hand and, eyes pleading, stepped back.

Dean's shoulders fell. She was right. The news of his father's illness could be kept quiet, but not for long. Word would eventually spread that their patriarch's health was in decline. He looked to his brother, worry deepening the lines on his face, and Dean again felt the familiar stab of guilt twist in his chest like a knife. It should be his burden to bear, the weight of the family's success or failure, not Sam's.

"Alright." He conceded weakly, stepping back as his mother's facial features shifted into something fierce.

"What about the Novaks?" Sam asked. "Dean and I should deal with them before the wedding."

"Yeah, I uh, I was gonna tell you, Sammy," Dean said, scratching the back of his head idly. "I talked to Rowena tonight. She gave me some intel on the family."

Mary looked at Dean with a mixture of pride and disappointment. "You shouldn't have gone to Rowena's alone." She said, her tone steely. "But the more information we have, the better. What did she say?"

"Something about them being god-fearing Catholics." He wracked his brain for the details of what Rowena had said. "Apparently, they're ruthless. The dad, Chuck, he all but ran Newark through altruism and selflessness if you can believe it. Left a decent trail of bodies him, though." He collapsed back into the chair next to his father's bedside. The sun would be rising soon, and Dean wished for nothing more than a hot shower and fresh sheets. "He built his family from adopted street kids, plus his own four sons and, get this, they're all named after archangels."

Sam snorted audibly. "So, what the hell are they doing here?"

"Beats me." Dean stretched his arms above his head. "But Rowena reckons that Chuck targeted Bela because of her art trade, and I'm thinking that's how we get to 'em."

Mary sat down in the chair next to Dean and laid her hand on his cheek warmly. Dean relaxed into the touch. "My sweet boy," she cooed. "My sweet, brilliant boy. You're so good. So smart." Dean all but glowed under her praise as she gently stroked the side of his face, caressing her fingers through the short hair at his temple.

"I can help with that." Jess piped up from where her head rested sleepily against Sam's chest. "My parents are holding an art auction in a few days. It's a charity fundraiser for some west coast non-profit, but they're expecting a big crowd. If the Novaks are involved in art at all, they'll be there. I could put Sam and Dean on the guest list..." She looked nervously between Mary and Sam.

Mary rose and walked slowly towards her new daughter-in-law before embracing her tightly. She pulled back and, though her eyes were tired, the smile she gave Jessica was warm and welcoming. "I knew you'd fit into the family, my dear." She released her and looked at Sam. "You made a good choice, son."

"Yeah," he said, squeezing Jess's shoulder into his ribs as he smiled sweetly down at her. "Yeah, I did."

"So, it's settled," Mary exclaimed, rubbing her hands together. "Dean, Sam, you two will go to the art auction with Jess and try to identify at least one member of the Novak family."

Dean stiffened. "Uh, actually, mom...there's something else I've gotta tell you..."

Mary's expression when she rounded on Dean was nearly unrecognizable from before. Her eyes, which had moments ago held the icy cold of resolve to protect her family, now burned with a fire of reproach that Dean felt pierce into his soul.

"What?" She asked, her tone too soft to be anything but terrifying.

"I, uh, I met one of them already. Tonight. At Lee's." He gulped as the fire in Mary's eyes flared, then dissipated. "Castiel. I assume he's one of the adopted kids."

"You spoke to him?" Mary asked.

"Yeah, he uh..." Dean hesitated for a split second. While his father may have been the one to teach him the meaning of fear, his mother was no less terrifying. "He helped me out of a tough spot with these two idiots picking a fight. He seemed nice." 

He fidgeted slightly, uncomfortable under his mother's gaze. She knew about his past relationship with Lee, even about the few nights he spent with a man named Aaron after he and Lee had split. While she had never been as violently against his trysts with men as his father, she had never openly expressed approval or support of them either.

"Did he know?" Asked Sam, breaking the tension of the moment. "That you're a Winchester, I mean."

"No." Said Dean, looking away from his mother's eyes. "I told him I was Dean Smith, Sandover sales associate. Didn't give him a reason not to believe me."

"That's good." Mary smiled devilishly at her son. "I assume you were _pleasant_ to him?" The question was a double-edged sword. Dean knew she was asking if he had flirted with Cas, used his looks and charisma to make his knees go weak, batted his eyelashes enough to make the man swoon, but if he admitted that openly now, here, in front of his family, there would be no going back.

He swallowed hard. "If you're asking me if I was polite, then yes." He said curtly. "If you're asking me if I made a move on him," Dean's eyes went dark, lips quirking up at the corners in a twisted grin. "Of course."

The glee in his mother's eyes made Dean's stomach turn. He knew that look. He had seen it once in his youth, moments before she had watched a man hang from a crane after selling out John to the police.

"It seems your proclivity for the company of men is not such a great shame to this family after all, Dean." She stated. There was no warmth in her voice, no notes of approval. Her glee did not come from a place of love for her child; it came from the cold, calculating mind of a mafia wife, willing to risk everything to protect her Family. "Did this, 'Castiel' return your advances?"

Dean let his grin deepen as his mother's intentions became evident in his mind. He could see her plan formulating, even as the gears turned in her brain. "He did."

"Then we can use that." Mary turned to Sam and saw the same sadistic glint in his eyes that filled hers. "Sam, you will go to the auction as Jessica's escort. Dean," she returned her eyes to her eldest son, "you will go as a representative from Sandover. I'll speak to the company and make sure they don't already plan on attending. You will find Castiel and woo him." She approached Dean and laid a hand on his shoulder. "You truly are my son. Your charm, your whims of sexual desire...you will make him fall for you. Make him weak." Mary smiled and removed her hand, moving to sit at John's bedside. She clasped her husband's hand in her delicate fingers and gazed lovingly at him. "And when he is weakened by love and lust, you will destroy the Novak family from the inside out."

"Yes, mother," Dean said through his smirk. He squeezed her shoulder assuringly and looked at his father. I will make you proud, he thought.

Jessica and the Winchester boys left the bedroom quietly, allowing their parents time together. They descended the stairs to the front room, discussing their plans for the art auction. They opened the front door and stepped into the brisk morning, bathed in the golden glow of the sunrise.

"I texted Benny for you." Said Sam. "He should be here soon."

"Thanks," replied Dean. He bent down and placed a light kiss to the top of Jessica's head. "Welcome to the family, sis."

She smiled up at him sleepily as the crunch of tires could be heard up the gravel drive, and Benny's SUV pulled into view. Dean bid his brother farewell as they parted ways. He climbed into the backseat and slumped down against the warm upholstery.

"You seem like you're in a better mood than a couple hours ago," Benny said, handing Dean a still hot take-out cup of coffee over the back of the seat. He glanced in the rearview mirror and, spying the menacing grin that remained hanging on Dean's lips, he groaned.

"What's that for?" Dean asked lazily, sipping at the blessed bitterness of the coffee as it warmed his insides and washed the weariness from his limbs, new purpose infusing his veins.

"Whenever one of you Winchesters gets that **look** on your face, it means I'm gonna have to dig some poor bastard's grave." He mused, pulling out of the driveway and onto the main road, navigating the car towards Dean's apartment downtown. "I swear you sick fucks enjoy the killing more than the luxury of your lives."

Dean chuckled and closed his eyes to the world for just a moment. "Well, what can I say, Benny?" He smiled despite himself. "It's pure, life and death. It's in my nature."

He let himself drift into a comfortable sleep as they sat in the morning traffic, the radio quietly playing Frank Sinatra's 'My Way' in the background. His dreams were filled with blue-eyed angels and bloody crowns of thorns, piercing flesh and wrapping around bone. How poetic that a family named for angels should be destroyed by a man who once thought he had the devil in his very soul. Dean smiled in his sleep at the thought.

He had work to do.

**Notes for the Chapter:**

> Well, I hope you enjoyed that! Poor John (not really), and yay Benny for being such a Good Friend. Things will start picking up in the next few chapters, I promise.
> 
> Come hang out with me on [Tumblr](https://www.tumblr.com/blog/bktynes-writes) if you'd like to. I pretty much live there :)

**Author's Note:**

> I hope you enjoyed reading chapter one! As I said, this is a work in progress so, kudos/comments are always appreciated, and if you'd like to follow me on tumblr, again, I'm [@bktynes-writes](https://www.tumblr.com/blog/bktynes-writes).


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